The present invention relates to epoxide derivatives of hydantoins having hydroxy aromatic substituents.
Hydantoins having hydroxyphenyl substituents are known. For example, South African Pat. No. 78/4416 teaches the preparation of 5-(p-hydroxyphenyl)hydantoins by reacting phenol with glyoxylic acid or a salt or ester thereof and urea in the presence of an acid catalyst in an aqueous medium. It is taught that the compound is useful as a precursor to p-hydroxyphenylglycine. Similarly, see Agric. Biol. Chem., Vol. 45, p. 831 (1981). Additionally, 5-(p-hydroxyphenyl)hydantoin is known from Harvill and Herbst, J. Org. Chem., Vol. 19, pp. 21-30 (1944), as being prepared by heating p-hydroxybenzaldehyde, potassium cyanide and ammonium carbonate in aqueous alcoholic solution. U.S. Pat. No. 3,939,175 teaches the use of p-hydroxyphenyl hydantoins and related compounds as stabilizers for organic materials such as polymers derived from olefins, vinyl compounds, .alpha.,.beta.-unsaturated acids, unsaturated alcohols or amines, epoxides or bisglycidyl ethers, and also for polyphenylene oxides, polyurethanes, polycarbonates, polysulfones, polyamides, polyesters, alkyd resins, and the like.
Dihydroxyphenyl hydantoins also are known. See, e.g., Chemical Abstracts 92:146767b and Chemical Abstracts 95:62703b.
Polyepoxides of hydantoins and related compounds have been prepared. See, e.g., U.S. Pat. Nos. 3,449,353; 3,631,221; 3,779,949; 3,821,243; 3,907,719; 3,975,387; 3,986,366; 3,925,407; 4,052,366; 4,209,608; 4,210,744; and 4,346,207. When said epoxy compounds are cured, they typically give cured resins having poor thermal stability.
Heretofore, polyepoxy hydantoins having epoxy aromatic substituents have not been disclosed. In view of the deficiencies of known polyepoxy hydantoins, it would be desirable to have an epoxidized hydantoin having improved thermal stability, as indicated by higher glass transition temperatures.